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Full text of "Practical Organic Chemistry"

APPENDIX

With nitrous acid the hydroxy-acid is formed,
/NH,                          OH

CH.2            + HNOo = CHo

XCOOH

PREPARATION 21.

Diazoacetic Ester.—The primary amines of the aliphatic
scries differ from those of the aromatic group in the fact that the
former yield no diazo-compounds with nitrous acid. It is other-
wise with the ammo-esters, the ester group probably furnish-
ing the acid character (represented by the nucleus in the aromatic
series) necessary to give stability to the compound. It should
be pointed out that the two classes of compounds have not an
identical structure. The formation of diazoacetic ester from
pyruvic ester and hydrazine and subsequent oxidation with mer-
curic oxide indicates that both nitrogen atoms are attached to
carbon,

CM:i\                                     C1I3X      ,NH

>CO + NIL.NHo ->            \c/1        -^

CII.O. OX              •"       "        CH,O.C(X    \NH

-N

In addition to the reactions described in the preparation
diazoacetic ester unites with uiisaturated acids and forms cyclic
compounds. Fumaric ester, for example, combines in the
following way : —

>     RO.OCHC/V             ^

COOK            CII.COOR           RO.OC.HC— 'CH.COOR

RO.CO.CH

I    \               +   Na.

KO.CO.CM— CM.COOR  .

When bisdiazoacetic ester is heated with water or dilute acid
it  breaks up into hydrazine and oxalic acid,

/N=N\                                  COOH

HOOC.CH<         >CH.COOH + 4HoO = 2 |

\N=N/                        "        COOH